Organic/inorganic hybrid materials such as organic siloxane compounds exhibit both characteristics of organic properties such as hydrophobicity derived from the organic group and inorganic properties such as hydrophilicity or high reactivity to water and condensational reactivity derived from a siloxy group. A functional material having various functions such as a refractive index control function, a light absorption function, a light emitting function, a charge transport function, etc. can be prepared through polymerization under sol-gel reaction conditions from such organic/inorganic hybrid materials such as especially the organic siloxanes containing a trialkoxysilyl group.
However, the organic/inorganic hybrid materials may not perform a desired silane coupling reaction with other functional groups due to the fact that tri-alkoxy silyl groups thereof tend to preferentially perform exchange reactions with alkoxy groups or silanol groups of other molecules or may be hard to perform sol-gel reactions due to the fact that tri-alkoxy silyl groups tend to perform hydrolysis reactions, when compared to polymerization reaction in which chemical products or reagents which contain no siloxane group are performed through condensation or polymerization. Furthermore the organic/inorganic hybrid materials is difficult to be purified by silica-gel chromatography and also difficult to be stocked for a long period of time, due to the fact that the hybrid materials being unstable to moisture and water. Accordingly, functional materials prepared from the conventional organic/inorganic hybrid materials are poor in yield, in production efficiency and purity.
In Non Patent Document 1, the inventors of the present invention disclose preparation of functional aryl (diallyl)ethoxy silanes which could be precursors in sol-gel reaction and disclose their palladium-catalyzed coupling reaction. Further, in Patent Document 1, the inventors of the present invention disclose a method for preparing an organic silica composite material such as a mesoporous body, etc. through hydrolysis and polycondensation reactions of an organic silane compound having allyl groups in a solvent.
Compounds containing a perfluoro group have a strong bond between a carbon atom and a fluorine atom, so that it has an excellent heat resistance and has further small coefficient of friction or low refraction index, due to the existence of fluorine atoms. Therefore, such compound containing the perfluoro group is used to give water- or oil-repellency, to exhibit a moderate lipophilicity, anti-reflective property and also to protect the surface of a substrate by forming a coating onto a surface of a base material or applying paint thereof. For example, in Patent Document 2, optical members that are made of a hardened material prepared from fluorine-substituted-alicyclic group-containing (meth)acrylic acid ester through heating or an active energy ray irradiation, are disclosed. In Patent Document 3, fine particles which are cross-linked with each other and are made of fluorine containing acrylic polymer which is modified by a crosslinkable functional group and hardened by the crosslinkable functional group, and an optical material containing the bonded fine particles are disclosed. In Patent Documents 2 and 3, a fluorine containing polymer is not chemically bonded directly to the various base materials such as silica particles, glass plates, metal plates, resin films, etc. Fluorine-containing polymers have poor scratch resistance and are easily scratched when contacted.
An organic silane compound which can be a silane coupling agent developing various functionalities has long been desired. Such organic silane compound has more reactivity than the conventional organic/inorganic hybrid materials; has reaction-specific, charge-specific, or stereo-specific property; can be induced from various starting compounds such as amino group-containing compounds; has moderate hydrophilic and hydrophobic properties and three-dimensional characteristics; and further has a moderate condensational or polycondensational reactivity to give functions to various raw materials. Further, a fluorine-containing organic silane compound, which can develop much better scratch resistance, can form a stronger bonding derived from a direct chemical bonding, and can develop moderate water repellency and oil repellency, has been desired. The layer of the fluorine-containing organic silane compound can be more excellent rather than a merely formed coating layer which is attached physically, through roughness of the surface and electrostatic attraction, to the surface of the base material such as particles, plates or film-like ones.